Hexane → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-trifluoromethylphenyl)oxindole
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].[Li]CCCC.CCCCCC.[CH2:23]([N:25]([CH2:44][CH3:45])[CH2:26][CH2:27][N:28]1[C:38]2[C:33](=[C:34]([C:40]([F:43])([F:42])[F:41])[CH:35]=[C:36]([I:39])[CH:37]=2)[C:31](=[O:32])[C:29]1=[O:30])[CH3:24]>C1COCC1>[CH2:44]([N:25]([CH2:23][CH3:24])[CH2:26][CH2:27][N:28]1[C:38]2[C:33](=[C:34]([C:40]([F:42])([F:43])[F:41])[CH:35]=[C:36]([I:39])[CH:37]=2)[C:31]([OH:32])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]([F:11])([F:10])[F:9])[C:29]1=[O:30])[CH3:45]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-bromobenzotrifluoride (0.3 mL, 2.23 mmol) in THF (1.5 mL) was added dropwise 1.53 N BuLi in hexane (1.45 mL, 2.22 mmol) over 10 min at −78° C. and the mixture was stirred for 10 min. The resulting solution (1.2 mL, 0.82 mmol) was then added dropwise to the cooled solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodoisatin (352 mg, 0.8 mmol) in THF (4 mL) at −78° C. via a syringe. The mixture was allowed to warm to room temperature and stirred for 30 min. The reaction was quenched with aqueous NaHCO3. The mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 50:1 to 40:1 chloroform/methanol to give the title compound (96.3 mg, 21%).
Workup
- stirringstirred for 30 min
- customThe reaction was quenched with aqueous NaHCO3
- extractionThe mixture was extracted with ethyl acetate
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography with 50:1 to 40:1 chloroform/methanol
Sources & evidence
- ORD record
- ord-b45bc991801a4aa0a5ab8d6175f73d6f
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06576656B1
Reaction notes
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